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• W3163043 endingPage "482" @default.
• W3163043 startingPage "451" @default.
• W3163043 abstract "Electrophilic substitution allows replacement of a proton or another electrofuge with a different group and is the most-used process for functionalizing aromatic rings, whereas nucleophilic substitution is often considered to be more difficult or to require special substituents or reaction conditions. Prior to 1970, only two significant classes of nucleophilic substitution processes on aromatic rings had been identified. The first, formally termed the SNAr reaction, requires the presence of one or more electronwithdrawing groups on the aromatic ring, and is a two step addition-elimination process (see Chapter 2.1 of this volume), whereas the second proceeds through the intermediacy of arynes in a two-step elimination-addition sequence and often is accompanied by cine substitution (see Chapter 2.3 of this volume). It was during a study of the latter reaction type involving treatment of 5- and 6-iodopseudocumenes with potassium amide in liquid ammonia that Kim and Bunnett1 observed that more of the respective ipso substitution products were being formed than could be explained on the basis that the reaction was proceeding through a common aryne intermediate. It was shown that the ipso substitution reaction was radical in nature and involved single-electron transfer steps, being inhibited by radical scavengers and promoted by one-electron donors, such as potassium. The reaction was recognized as being an aromatic analog of substitution processes at the aliphatic carbon in p-nitrobenzylic and α-nitroalkyl halides, independently identified in 1966 by the research groups of Kornblum2 and Russell.3 Bunnett>1,4 suggested the term ‘Srn1’, standing for substitution, radical nucleophilic, unimolecular, for these reactions and this widely adopted description will be used throughout this chapter." @default.
• W3163043 created "2016-06-24" @default.
• W3163043 creator A5037589297 @default.
• W3163043 date "1991-01-01" @default.
• W3163043 modified "2023-10-07" @default.
• W3163043 title "Nucleophilic Coupling with Aryl Radicals" @default.
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